The 2020-21 MLB Offseason: Dates, Deadlines, What and When to Expect Things for the Cubs

Social Navigation

The 2020-21 MLB Offseason: Dates, Deadlines, What and When to Expect Things for the Cubs

Chicago Cubs

They said it before the 2018 offseason. They said it again before the 2019 offseason. BUT THIS TIME THEY MEAN IT.

I kid about the Cubs front office’s take on the state of the roster after more or less running the thing back three years in a row, but it is true that this group clearly needs significant change. It’s also true that, thanks to the timelines on player control, the relative competitiveness of the Cubs and the NL Central, and the financial impact of the pandemic, I suspect we’re gonna see the Cubs mostly run it back once again.

Either way, there’s a whole lot ahead for the Cubs this offseason, where the opportunities for significant change certainly will not be in short supply.

But what exactly is “the offseason”? What does it include? What happens when? When do we expect what?

With the World Series set to begin next week, the offseason is coming later this month. So now seemed a wise time to lay out a roadmap of the important dates, deadlines, and timelines on the things that will be taking place in the coming months of “the offseason.” (Note: we have to use some approximations for dates not yet announced, or dates tied to the undetermined end of the World Series.)

October 29 – The day after the World Series ends, players eligible for free agency become free agents. The Cubs will have at least 10 free agents:

LHP Andrew Chafin, 30

RHP Tyler Chatwood, 30

UTL Daniel Descalso*, 33

OF Billy Hamilton, 30

RHP Jeremy Jeffress, 33

2B Jason Kipnis, 33

LHP Jon Lester*, 36

OF Cameron Maybin, 33

C Josh Phegley, 32

LHP Jose Quintana, 31

*options decisions due, but locks to become free agents

Note that this does not include Anthony Rizzo, on whom the Cubs have a $16.5 million team option for 2021 ($2 million buyout, so it’s a $14.5 million decision), which I believe they will exercise. This also does not include players who are controlled via arbitration but who may well be non-tendered later in the offseason and at that point become free agents.

October 29 through November 2 – Although players are immediately free agents after the World Series concludes, they cannot sign with a new team for five days. So, while teams can start reaching out to agents, no new contracts can be inked. This five-day period, then, serves as something of an exclusive negotiating window for teams with departing free agents. Usually you don’t see too many deals struck at this time, but it does happen very occasionally. Does the pandemic financial situation make deals in this period more or less likely? I could probably make the argument in either direction – we know teams will feel risk-averse, but will players, too? If so, you could see some one-year, low-dollar deals inked for players to return to their former teams.

November 1-2 – Options are due around five days after the World Series (it’s actually specified in the player’s contract, but it’s usually right around here). Depending on decisions around baseball, the free agent pool could be further increased. There is also sometimes trade activity in the days leading up to the option decision date (because, for example, Team X might have an option on Player A that they don’t want to pay, but Team Y definitely does want Player A at that option price – so the two teams consummate a trade at the last minute where Team X picks up the option, and then deals Player A to team Y).

The Cubs have several options decisions that will impact their free agents, as noted above. These players will not fully join free agency until the options decisions are made.

November 2 – At the end of that five-day window following the World Series, teams must make decisions on whether make a “qualifying offer” to free agents – in short, in order to receive draft pick compensation should a free agent sign with a new team, his former team must first offer him a one-year deal worth the average of the top 125 salaries in MLB from the previous year. The qualifying offer amount is expected to be around $18.9 million this year. If a player receives a qualifying offer, he can accept it, negotiate a different deal with his former team, or sign with another team, costing that team a pick (or picks) in the 2021 Draft, and pool space in IFA.

The Cubs will not be making any qualifying offers this year, as there are not even any close calls (regardless of the financial market). League-wide, it’s possible there will be surprisingly few QOs this year.

Approximately November 2 to March 2021 – The “Offseason.” The “Hot Stove.” The “Lukewarm Stove.” Whatever you want to call it, this is the meaty period where a team’s roster is built for the subsequent year via free agency, trades, tender decisions, minor league decisions, etc. Generally speaking, the hottest period is from about mid-November until mid-January, but there’s always a ton of stuff that happens outside of that window, too. In fact, in recent years, activity has been pushed later and later, with more of the action in the January to March window than typical.

November 9 to November 12 – Nothing to see here. Historically, there was a week of GM Meetings and Owners Meetings early in the offseason, but as a physical gathering, these have obviously been cancelled. Whether there will be remote meetings – and what it would mean to we outside observers if there were – is still kinda up in the air. I would think the Owners Meetings portion will proceed, though, as there will be league business to conduct (that could include some rules decisions).

Teams often conduct organizational meetings around this time, too, but again, that can be done virtually at this point. And it can be done whenever. So, yeah, lots of uncertainty about this one.

Approximately November 12 – Players must decide whether to accept the qualifying offer by this date (they used to have just seven days after receiving a QO, but that’s since been increased to ten days). Big-time free agency won’t really get going until after this date, and even that’s on the early side.

November 3 to November 14 – The various MLB awards are announced, starting with the Gold Gloves and concluding with the MVPs. These dates are not necessarily official just yet, but we’ve received no word that the timing will be changed. Yu Darvish’s Cy Young hopes will be the big story of awards season around here.

November 20 – A team’s 40-man roster must be set for the purposes of the Rule 5 Draft (i.e., players already in the organization that the team would like to protect must be added by this date). The Cubs will purge some names from the 40-man roster over the coming weeks, partly to open up spots for Rule 5 purposes. From there, the Cubs will decide on a few young players to add to the 40-man so that they cannot be selected in the Rule 5 Draft (about which, more below).

December 2 – Deadline for tendering contracts to players under team control but not signed for 2021 – i.e., players in their first three years of service time who can be “renewed,” and arbitration-eligible players (players with three or more years of service time, but fewer than six years of service time). This decision will include Kris Bryant, Javy Báez, Kyle Schwarber, Willson Contreras, Albert Almora, Kyle Ryan, Ian Happ, Jose Ramirez, Victor Caratini, Colin Rea, Ryan Tepera, Dan Winkler, and Rex Brothers. Yes, the Cubs have a lot of arbitration-eligible players. Note that tendering a contract to these players is optional. Players shy of arbitration level service time are also sometimes non-tendered by this date.

December 6 to December 10 – The Winter Meetings in Dallas, Texas … maybe. The event hasn’t officially been cancelled yet, but the pandemic makes it highly unlikely that in-person meetings will proceed as normal. There is business to conduct at the meetings, so there will be SOME version, but it’s probably not going to look like years past.

Historically, the gist: MLB executives, agents, and players (as necessary) get together for a week. The Winter Meetings are a notable source of rumors, signings, trades, etc. While not all of the big offseason moves go down at the Meetings, there’s always a ton to discuss (not only amongst ourselves, but also amongst those MLB executives, agents, and players). In short, it’s an exciting time for folks who love rumors – like a mini version of the Trade Deadline, but spread out over four days. It’s not quite a Blogathon around here, but it’s pretty close, and we do find ourselves waking up at 3am to quickly check in and make sure nothing is breaking.

December 10 – The Rule 5 Draft. Players who’ve been in an organization’s system for a while (several years) without yet reaching the 40-man roster are eligible to be selected by other teams for a small fee, placed on that team’s 25-man roster, and then kept for good if the player can stick on the 25-man roster for almost all of the subsequent season. Typically, in this draft, rebuilding clubs do some selecting, and competitive clubs do some sweating. In the current environment, it wouldn’t at all be surprising to see this year’s Rule 5 Draft even more aggressive than usual.

You can see the full list Cubs players eligible for the Rule 5 Draft over at TCR. The Cubs should be able to protect upwards of five or six, if they so choose, but historically you see about three or four prospects rostered before the draft. It depends on talent, on which guys are likely to be selected, and on how much 40-man roster space you need for other moves. (We dig in deeper on the prospects as the rostering deadline on November 20 approaches. For now, the Cubs have already added Brailyn Marquez, who otherwise would’ve been Rule 5 eligible this year.)

Approximately December 12 to January 31, 2021 – This is about the time that the Cubs will be sending out non-roster invitations to 2021 Spring Training. The invitations go to prospects and players in the Cubs’ system who’ve not yet been placed on the 40-man roster, as well as veterans who are looking for a 2021 job, but have to “prove it.” You will roll your eyes at most of the minor league free agent non-roster invitees, but it doesn’t hurt to grab as many of the best as possible – and sometimes it pays off. The Cubs got a lot out of some of their non-roster relievers this year, and Jason Kipnis was also a non-roster invitee.

January 15, 2021 – This is when teams and arbitration-eligible players will submit arbitration requests (each side picks a number – we’ll have more on those details when the dates approach), and then hearings will be set, if necessary, for early February.

January 15 to January 17, 2021 – The Cubs Convention … is not happening. Thanks to the pandemic, CubsCon 2021 has already been cancelled. Maybe next-next year. Fans will get a chance to see, meet, and hear from Cubs players, coaches and management, and the Cubs frequently like to use the Convention as an opportunity to introduce a big offseason acquisition to the fans. You can keep tabs on passes here. It figures to be a fun and busy event, as always.

Approximately February 16, 2021 – Pitchers and catchers report to Spring Training, and your heart climbs up into your throat once again, not to depart for (hopefully) another eight and a half months. That, of course, presumes the 2021 season is expected to begin on time. Given the state of things, and the possibility that MLB may want to push things back to increase the chance that fans can be at games, the start of Spring Training could get bumped.

Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.